Phosphorus oxychloride → HCID 19029125, compound

HRID 1867372Notes

Reaction equation

HRID 1867372 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([NH:19][NH:20][C:21](=[O:23])[CH3:22])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[O:23][C:21]([CH3:22])=[N:20][N:19]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68432913HCID 68432913, compound

Product 1

HCID 19029125HCID 19029125, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2.00 g (6.26 mmol) of 4-(N′-acetyl-hydrazinocarbonyl)-piperidine-1-carboxylic acid benzyl ester in 30 ml acetonitril was treated at RT with 0.69 ml (7.51 mmol) of phosphoroxychloride. The suspension was stirred 1 h at RT and the refluxed for 2 h, evaporated, dissolved in CH2Cl2 and neutralized with aqueous saturated NaHCO3 solution. The aqueous phase was extracted with CH2Cl2 (2×). The organic phase was dried (Na2SO4) and and evaporated to give after flash silica gel column (EtOAc) 1.69 g (89%) of the title compound as light yellow oil. MS: 302.1 (MH+).

Workup

  1. temperaturethe refluxed for 2 h
  2. customevaporated
  3. dissolutiondissolved in CH2Cl2 and neutralized with aqueous saturated NaHCO3 solution
  4. extractionThe aqueous phase was extracted with CH2Cl2 (2×)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-39d4b9f2bb9e490a8ba19d8ba09d1974
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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